1-Bromo-2-Chloroethane → 1-(1H-Indol-3-yl)cyclopropanecarbonitrile

HRID 445136

Reaktionsgleichung

Reaktionsgleichung von HRID 445136
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1.[CH:13]([N-]C(C)C)(C)[CH3:14].[Li+].BrCCCl>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2([C:11]#[N:12])[CH2:14][CH2:13]2)=[CH:2]1

Komponenten

5

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 351795Indole-3-acetonitrileHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 153783241-(1H-Indol-3-yl)cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

1H-indole-3-ylacetonitrile (18.7 g) was dissolved in tetrahydrofuran (240 mL) and, after cooling to −30° C., lithium diisopropylamide (2.0M heptane/tetrahydrofuran/ethylbenzene solution, 240 mL) was added dropwise, followed by stirring at −5° C. for 30 minutes. The reaction mixture was cooled to −30° C. and 1-bromo-2-chloroethane (11.0 mL) was added dropwise, followed by stirring for 2 hours while heating to 0° C. The reaction mixture was poured into ice/hydrochloric acid (2N, 360 mL) and extracted with ethyl acetate. The organic layer was washed in turn with water, an aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain a compound and the compound was recrystallized from (hexane:ethyl acetate=1:1) to obtain the titled compound having the following physical properties (8.67 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to −30° C.
  2. stirringby stirring for 2 hours
  3. temperaturewhile heating to 0° C
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed in turn with water
  6. dry with materialan aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)
  9. customto obtain a compound
  10. customthe compound was recrystallized from (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f08f170c81f44a6eb2665abafbddf2c2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476293B2

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